A Boy and His Airline

He walks through airports dressed like Elvis. He paints his planes to look like killer whales. He’s Southwest’s Herb Kelleher, and because of him Texas’ psychic landscape will never be the same. 

Let’s do a Dr. Ruth spoof,” says Herb Kelleher, jumping to his feet in a spasm of creativity. Kelleher is brainstorming with three of his top managers in his cluttered Southwest Airlines office near Dallas’ Love Field. The task at hand is to come up with skit ideas for an airline-industry conference. Kelleher envisions a scene in which Dr. Ruth would be on the telephone talking to Robert Crandall, the abrasive head of Dallas-based American Airlines, which has just become the largest domestic carrier. “Remember. Bob,” Kelleher says, mimicking the tiny sex doctor, “size isn’t everything.”

The focus shifts to New York deal-maker Donald Trump and his attempt to purchase the Eastern Airlines Shuttle, which runs between Boston, New York, and Washington. Someone suggests a musical parody: “The Lady is a Trump.” Then Kelleher lights on the battle for the entertainment-park business. Kelleher’s own Southwest Airlines could be creative fodder for this one; in 1988 it became the official airline of Sea World. Delta has Disneyland and Disney World. Kelleher suggests taking a poke at United, which not only does not have an affiliation but also just lost its place as the largest airline. “Why not make United the official airline of Popeyes fried chicken?” he suggests.

The meeting epitomizes the Kelleher personality: his irreverence, his spontaneity, his zaniness, and, most of all, his competitiveness. The airline he helped found and now runs is a direct extension of that personality—Kelleher himself often stars in the company’s offbeat commercials. In an industry beset by turmoil and takeovers, Southwest thrives by making its own rules.

At 57, Kelleher looks and acts like a first-generation astronaut, a hard-driving, hard-drinking, fast-living sort of guy

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